HCID 86705357, compound → HCID 68090513, compound

HRID 1773651Notes

Reaction equation

HRID 1773651 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:24][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])[C:5]2[N:6]([C:8]([C:11]3[CH:22]=[CH:21][C:14]([C:15]([NH:17][CH:18]4[CH2:20][CH2:19]4)=[O:16])=[C:13]([CH3:23])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.Br[Mg][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[CH2:34]>C1COCC1>[CH:18]1([NH:17][C:15](=[O:16])[C:14]2[CH:21]=[CH:22][C:11]([C:8]3[N:6]4[N:7]=[C:2]([C:33]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH2:34])[CH:3]=[C:4]([NH:24][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])[C:5]4=[N:10][CH:9]=3)=[CH:12][C:13]=2[CH3:23])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 86705357HCID 86705357, compoundHCID 178462449HCID 178462449, compound

Product 1

HCID 68090513HCID 68090513, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 24 mg (50 μmol) 4-{6-bromo-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-b]pyridazin-3-yl}-N-cyclopropyl-2-methylbenzamide which was prepared according to intermediate example 247a in 1 mL THF is dropwise added 1.0 mL (0.5 mmol) of a 0.5 M solution of bromo(1-phenylethenyl)magnesium in THF at rt. After stirring overnight at rt, the mixture is heated at 50° C. and stirred for 3 more days to give after working up and purification 1.7 mg (5%) of the title compound.

Workup

  1. customat rt
  2. temperaturethe mixture is heated at 50° C.
  3. stirringstirred for 3 more days
  4. customto give
  5. custompurification 1.7 mg (5%) of the title compound

Sources & evidence

ORD record
ord-311d6a06126e4908a4c0f6bdb2c2665f
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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